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Synthesis, antimicrobial activity and docking studies of new N-ethyl-3-indolyl heterocycles

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An Erratum to this article was published on 28 January 2016

Abstract

We report here, the synthesis of 1-(1-ethyl-1H-indol-3-yl)-3-pyridin-4-yl-prop-2-en-1-one (2) which was used as a base to the synthesis of new 3-(pyrimidin-4-yl)-1H-indole derivatives; their thioglycoside and N-glycoside derivatives 3–10a, b; pyrane derivatives and pyranopyrimidine derivative 11–13; and tricyclic pyranotriazolo[1, 5-a]pyrimidine 14. Moreover, reaction of N-ethyl-3-acetylindole 2 with phenylhydrazine and hydroxylamine hydrochloride gave pyrazolyl-indole and oxazolyl-indole derivatives 15 and 16, respectively. The structures of the products obtained were confirmed by elemental analysis, IR, 1HNMR and 13C NMR. The newly synthesized compounds were investigated for their antimicrobial activity, and some of them showed high growth inhibition activities. Anti-bacterial activity of the synthesized compounds was further analyzed by the molecular docking approach, a method of simulation of fitting ligands into binding site(s) of macromolecular targets. AutoDock Vina results showed that compounds 5a and 6a, b were located in a pocket in the active site.

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Acknowledgments

The authors would like to thank Dr. El-Sayed E. Mostafa, Department of Microbial Chemistry, National Research Center, Cairo, Egypt, for performing the antimicrobial activity of the synthesized compounds.

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Authors and Affiliations

  1. Photochemistry Department, National Research Centre, 12622, Dokki, Giza, Egypt

    Weal A. El-Sayed, Hebat-Allah S. Abbas & Randa E. Abdel Mageid

  2. Chemistry Department, College of Science, King Khalid University, Abha, Saudi Arabia

    Hebat-Allah S. Abbas

  3. Molecular Networks GmbH - Computerchemie, Henke-str. 91, 91052, Erlangen, Germany

    Tomasz Magdziarz

Authors
  1. Weal A. El-Sayed
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  2. Hebat-Allah S. Abbas
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  3. Randa E. Abdel Mageid
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  4. Tomasz Magdziarz
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Correspondence to Hebat-Allah S. Abbas.

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The authors report no conflicts of interest. The authors alone are responsible for the content and writing of this article.

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Tomasz Magdziarz on leave from Institute of Chemistry, The University of Silesia, Katowice, Poland.

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El-Sayed, W.A., Abbas, HA.S., Abdel Mageid, R.E. et al. Synthesis, antimicrobial activity and docking studies of new N-ethyl-3-indolyl heterocycles. Med Chem Res 25, 339–355 (2016). https://doi.org/10.1007/s00044-015-1488-4

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